


A Second Round

by Notmenotthem



Category: Supernatural
Genre: Cowgirl Position, Demonic Possession, F/M
Language: English
Status: Completed
Published: 2020-09-25
Updated: 2020-09-25
Packaged: 2021-03-07 21:14:13
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,726
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26644327
Author URL: https://archiveofourown.org/users/Notmenotthem/pseuds/Notmenotthem
Summary: No one knows about Dean and Ruby. Ruby sleeps with Dean because he reminded her of her lost love. Neither one ever told Sam.
Relationships: Ruby/Dean Winchester
Kudos: 1





	A Second Round

Ruby moaned as Dean thrusted into her. This body, it was different from her old vessel, but Dean didn't mind. He swore to never tell Sam or Castiel. They slept together once, last year. It was a few days before Dean's deal was due. Ruby had come to Dean warning him about Lilith. Dean was terrified. He hid his fear.

Ruby came to Dean helping him kill Lilith's demons. It was a tough fight, Dean was outnumbered. But when the last demon fell, they were breathing hard. Dean wanted to go home and drink till morning. Ruby said a sarcastic remark and Dean slapped her. The next thing they knew they were fucking in the Impala.

Dean ripped off her jacket and threw it on the ground. Then he pulled down her jeans and boots and Ruby stripped the rest of her clothes off. Then they went in the backseat and fucked. Dean was wearing his clothes, except his shorts. His jeans and underwear were pulled down as he trusted into her tight body. Ruby swore this girl was dead. She killed herself with sleeping pills. Dean didn't ask why, but Ruby told him anyway. She suffered from the hands of her abusive boyfriend. He did something to her and abandoned her in her time of need. Ruby swore she wasn't in Hell. But in the inbetween. Her soul was guaranteed to have a ticket upstairs. Her ex, not so much.

Ruby groaned as Dean hit her sweet spot. As a demon, she was aware of her vessel's touch. She kissed Dean as he moved harder. 

"Mmm. Winchester."

"Shut up and kiss me."

Ruby was on top of Dean as he thrusted up. Her blond hair hanging down her face. She was going to give Dean a night he will never forget. Dean grabbed her nipples as she rode his dick. She liked Sam as well, but Dean reminded her of her lost love. She didn't lie about remembering, she did. He was a Winchester as well.

That was when she was still human. He was a witch hunter. He was the one to kill Ruby. Not that he wanted to, but it was either him or the dogs. They cried when her final night came. They knew each other when she was still human. He rescued her from being burned. 

There was a bounty on her head. The guy named Jonathan Winchester was a young up and coming hunter. He met Ruby when she was arrested for practicing witchcraft. Her lover, Ashley Goode betrayed her to the town council. She didn't know she was a demon. 

He was ordered to guard her from escaping. She wouldn't run. She was devastated that she was backstabbed. But that isn't why she was afraid. The gift Ashley gave her. It cost her eternal damnation. Ashley claimed she found a old book. Matilda, Ruby's old name was intrigued. 

Matilda was fascinated by what the book claimed. That it will give her any gift she ever desired. Money, safety, a big house. Love. Matilda had one. Ashley. Matilda loved Ashley. When they met, Matilda thought she was amazing. She was smart and beautiful. Matilda didn't care about her being a woman. 

As much as she liked Ashley, she knew homosexuality was illegal. They were put on trail, then sentenced to be hanged. The crime, being bewitched. Matilda knew it was dangerous, but she was intrigued. They started off as friends, then slowly became more.

She was terrified of the book Ashley gave her. But the sickness was coming to her town. Already most of the surrounding villages were dead or abandoned. The smell of smoke was familiar. Whatever that sickness was, it was contagious. You were dead in days. The townsfolk called it "Black Death."

To stop the sickness, they burned down entire neighborhoods, towns as well. To make sure the sickness wouldn't spread, they made the agonizing decision to kill the living survivors who were still alive. They pretended not to hear the screams. Poor things were burned alive. 

Her parents were dead. Thankfully not from the sickness, but from their carriage crashing. The horses were spooked by something and her father lost control. They both broke their necks. Matilda was devastated. At fourteen she wasn't ready to be a adult. Thank god her aunt took her in. It was two years later when she met Ashley.

She was gorgeous. Long black hair, big green eyes and a sharp wit. Matilda was in love. Her aunt didn't mind, she wanted her niece to be happy. Her step uncle, not so much. He was trying to marry her off to his best friend, Simon Ketch. Ugh. He was fifty five years old. Matilda was only sixteen. Yuck. 

She and Ashley started off as friends. When she told Ashley about her step uncle's plan to marry her off, Ashley swore she can get her out of it. A week later, her uncle and Simon were dead. Attacked by wild animals. Her aunt was devastated, but secretly Matilda was relieved. Robert was abusive and a drunk. He said if Matilda wasn't already engaged, he was going to take Matilda as his second wife to bear his children, since Victoria was barren.

When she heard of the sickness, she was terrified. Her aunt wasn't feeling well those days and Matilda was terrified. If the council ever found out, she'll be isolated for "treatment." Code for killed. She loved Victoria as a mom, and when she confided in Ashley about what what might happen, Ashley told her she can get her adopted mom and her out of the village. All she needed to do is to make a deal. 

At first Matilda said no. She knew Ashley was a witch, she caught Ashley practicing the dark arts. When confronted, Ashley admitted she has no choice. In her old village everybody died from the sickness. She was the lone survivor thanks to the book. When confronted, Ashley ran. Matilda asked why she couldn't save anyone else. Ashley said she couldn't. The book was meant for her, and only her. It was later that Matilda found out Ashley slaughtered everyone for her spell. To raise her master, The Dark Prince. Lucifer. It would take centuries though. This was just the beginning.

Day by day her aunt got sicker. When the neighbours started getting suspicious, is when Matilda made a desperate decision. She said she take the deal. That night she became a witch. She healed her aunt and she sent her away to Spain. Her and Ashley became lovers.

Then Ashley betrayed her. She left in the middle of the night and left behind "evidence." Chicken feet, a monkey's paw, and deer bones. She even left satanic symbols in the room. Matilda woke up to shouts. The council arrested her for witchcraft. Seeing the evidence, Matilda knew she was screwed. She was angry. Not at the council, but Ashley. She betrayed her.

Her trail lasted an hour. Matilda said nothing in her defense, they were right. But she didn't care. Her aunt was safe and healthy. She met the eyes of her jailer, Jonathan. He stared sympathetically at her knowing what happened. When she heard her sentence, she cried. She was going to be burned by sundown. 

She and Jonathan met at the jailhouse. She was there for three days. Jonathan Winchester was a good man. He was the same age as Matilda. He was different from Ashley. Dark blond hair, green eyes and a kind smile. Matilda wished she met him first. They talked for three days. The day she was going to be burned, Jonathan wasn't there. Matilda was saddened. The one guy that understood her. 

She said nothing when she was tied to the stake. Matilda prayed for it to end quick. Before the pyre was lit, there was the sounds of hooves, then a gunshot, then screams. As the townsfolk scrambled, a masked man came charging in. He took out a blade and cut her ropes. Then he lifted her and threw her on his horse. He pushed his horse hard. The sounds of guns behind her. A arrow narrowly missing his head. 

Seeing his eyes Matilda knew it was Jonathan. He saved her life. They ran to Italy where they lived together for ten years. 

They were happy. She tried not to think about her ticking clock. He didn't mind her practicing magic. He figured white magic would be helpful. Matilda only used it for helping people. Healing their sickness or helping them turn their luck around. They moved often, always changing names. When the night her deal was due, they cried. She was terrified. She begged Jonathan to continue his work. Ashley was still out there. He promised. He killed her before the hellhounds came. Her soul went to Hell.

Now that she was a demon, she was glad Dean killed Astaroth aka Ashley. Jonathan couldn't find her, she disappeared back to Hell. She was sent back to Hell by another hunter, Jacob Turner. When she saw her again, she tried to distract her so she can plan her revenge. Unfortunately, she saw right through her. Thankfully Dean killed her. Matilda, now called Ruby was thankful. She dreamed about revenge for eons. 

She sighed when Dean exploded. Dean didn't care she was a demon. Sex was sex. Ruby smiled at Dean and promised him she'll keep this a secret. They got dressed and never mentioned it again. Now five months later they were having a sequel. 

Ruby moaned as Dean was moving inside of her. Dean was horny. He was in Hell for forty years and was getting frustrated. He had no clue she and Sam were lovers. Ruby smirked. This was the third Winchester she seduced. Sam's personality reminded her of Jonathan, but other than Dean's short hair, Dean was a dead ringer for his ancestor. Jonathan's was long and wavy. 

She cried out Jonathan's name. Neither Sam or Dean never minded. As she layed in Dean's arms, she pretended she was with Jonathan. She still remembered. But now as a demon, she had a task. Free Lucifer. Her and Dean got dressed and never mentioned it again. Poor Sam was falling hard for her. 

Sam was handsome and kind, but he wasn't Jonathan. But Dean was close enough.


End file.
